Condensed cyclic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11818951-B2
Application number	US-201916678508-A
Country	US
Kind code	B2
Filing date	Nov 8, 2019
Priority date	Feb 8, 2019
Publication date	Nov 14, 2023
Grant date	Nov 14, 2023

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and comprising an emission layer; and at least one condensed cyclic compound represented by Formula 1-1, 1-2, or 1-3:

where in Formulae 1-1 to 1-3, at least one of R 1 (s) is an electron withdrawing group, at least one selected from R 2 (s) and R 3 (s) is an electron withdrawing group, and at least one selected from R 4 (s), R 5 (s), and R 6 (s) is an electron withdrawing group, wherein a case where the number of cyano groups in the electron withdrawing group included in the condensed cyclic compound represented by Formula 1-1 is two or more is excluded.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an organic layer between the first electrode and the second electrode and comprising an emission layer; and
at least one condensed cyclic compound represented by Formulae 1-1A to 1-1F, 1-2A to 1-2G, and 1-3A to 1-3H:

wherein, in Formulae 1-1A to 1-1F, 1-2A to 1-2G, and 1-3A to 1-3H,
D 1 to D 5 are each independently selected from groups represented by Formulae 2-1 to 2-3,
in Formulae 1-1A, 1-1B, 1-2A to 1-2C, and 1-3A to 1-3C, D 1 and D 2 are different from each other,
in Formulae 1-1C, 1-1D, 1-2D to 1-2F, and 1-3D to 1-3F, at least two selected from D 1 to D 3 are different from each other,
in Formulae 1-1E, 1-2G, 1-3G, and 1-3H, at least two selected from D 1 to D 4 are different from each other,
in Formula 1-1F, at least two selected from D 1 to D 5 are different from each other,
b12 is an integer from 1 and 2,
b13 is an integer from 1 to 3,
b14 is an integer from 1 to 4,
b15 is an integer from 1 to 5, and
R 1 to R 6 are each independently selected from an electron withdrawing group, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
at least one of R 1 (s) is an electron withdrawing group, at least one selected from R 2 (5) and R 3 (5) is an electron withdrawing group, and at least one selected from R 4 (5), R 5 (5), and R 6 (5) is an electron withdrawing group,
wherein a case where the number of cyano groups in the electron withdrawing group included in the condensed cyclic compound represented by any of Formulae 1-1A to 1-1F is two or more is excluded, and

A 1 to A 4 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
L 1 to L 3 are each independently selected from a single bond, a substituted or unsubstituted C 5 -C 60 carbocyclic group, and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a1 to a3 are each independently an integer from 1 to 3,
Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
X 1 is selected from C(R 15 )(R 16 ), Si(R 15 )(R 16 ), N(R 15 ), O, and S,
R 11 and R 12 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
at least one selected from R 11 and R 12 is selected from a substituted or unsubstituted C 1 -C 60 alkyl group and a substituted or unsubstituted C 6 -C 60 aryl group,
R 13 to R 16 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
R 15 and R 16 are optionally linked via a single bond, C(Q 34 )(Q 35 ), Si(Q 34 )(Q 35 ), N(Q 34 ), O, or S,
b11 to b14 in Formulae 2-1 to 2-3 are each independently an integer from 1 to 5,
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium,

Assignees

• Samsung Display Co Ltd

Inventors

• Park Hyejeong

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title